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The Carcinogenicity of 3-Methoxy-4-aminoazobenzene and Its N-Methyl Derivatives for Extrahepatic Tissues of the Rat^*

( McArdle Memorial Laboratory for Cancer Research, Medical School, University of Wisconsin, Madison, Wis.)

In contrast to all previous results with many derivatives of 4-dimethylaminoazobenzene, the ingestion by the rat of 3-methoxy-4-aminoazobenzene or its N-monomethyl or N,N-dimethyl derivatives was found to induce high incidences of squamous-cell carcinomas of the ear duct. 3-Methoxy-4-aminoazobenzene also induced low incidences of adenocarcinomas in the small intestine and mammary gland. In addition, the 3-methoxy dyes induced a few solitary tumors of the skin. However, these dyes exhibited very little carcinogenic activity toward the liver. No tumors were noted in rats fed 2-methoxy-4-aminoazobenzene or its N-monomethyl and N,N-dimethyl derivatives, 2-hydroxy-4-monomethylaminoazobenzene, or 2-hydroxy-4-dimethylaminoazobenzene. Syntheses are described for five new dyes: 2-methoxy-4-aminoazobenzene; 2-hydroxy-, 2-methoxy-, and 3-methoxy-4-monomethylaminoazobenzene; and 2-methoxy-4-dimethylaminoazobenzene.

^* This investigation was supported by Grant C355 of the National Cancer Institute, United States Public Health Service, a grant from the Jane Coffin Childs Memorial Fund for Medical Research, and the Alexander and Margaret Stewart Trust Fund. We are grateful to Mr. Herbert Schmidt for valuable technical assistance.

Received 5/11/61.

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